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  • Title: Synthesis and structure-activity relationships of novel 2',2'-difluoro analogues of docetaxel.
    Author: Uoto K, Ohsuki S, Takenoshita H, Ishiyama T, Iimura S, Hirota Y, Mitsui I, Terasawa H, Soga T.
    Journal: Chem Pharm Bull (Tokyo); 1997 Nov; 45(11):1793-804. PubMed ID: 9396156.
    Abstract:
    To investigate the role of the 2'-hydroxy group at the C-13 side chain of docetaxel in the antitumor activity, we prepared several 2',2'-difluoro derivatives of docetaxel and evaluated their cytotoxicity against mouse leukemia and human tumor cell lines and their microtubule disassembly-inhibitory activity. These analogues were prepared by esterification of protected 10-deacetylbaccatin III (21) with appropriate alpha, alpha-difluorinated carboxylic acids (Charts 1 and 2). Among these 2',2'-difluorodocetaxel derivatives, 2',2'-difluorodocetaxel (23b) was approximately 3-10 times as active as 2'-fluorodocetaxel (29a) in terms of cytotoxicity. In addition, the 3'-(2-furyl) (23h) and 3'-(2-pyrrolyl) (23p) analogues showed activity comparable or superior to that of docetaxel (2).
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